Abstract
Tow types of nucleoside derivatives have been synthesized. To prepare the first type 1′,3′ ,4′,6′ -Tetra-O-benzoyl-β-D-fructo furanose (F1)with a free hydroxyl group at position-2′ was chosen as the Chiron. The compound (F1) can be easily obtained from the reaction of anhydrous D-Fructose with benzoyl chloride in pyridine. When (F1)was treated with 45% hydrogen bromide it gave 1′ ,3′, 4′, 6′-Tetra-O-benzoyl-β-D- fructo furanose bromide(F2).The bromo fructo benzoate (F2) was then reacted with the proper nitrogen base (Theophylline, Adenine, Benzimidazole, Benztriazole) to give the nucleoside analogues derivatives(F5), (F8), (F11)and (F14) by hydrolysis of the benzoate groups of (F6), ( F9), ( F12) and (F15). The newly synthesized nucleoside analogues, Guanosine nucleosides were reacted with Palmitoyl chloride in pyridine at (-12°C) to give the 6′ -O-palmitoyl, (F7), (F10), (F13) and (F16). The prepared nucleoside derivatives were characterized from their elemental analysis and IR, 1H-NMR and UV spectral data.
Highlights
Natural nucleosides and nucleotides play a key role in many biosynthesis and regulatory processes in the living cell (Marry, 1993)
The purine and pyrimidine nucleotides serve as monomeric units of RNA and DNA, an energy transcription (ATP); parts of coenzymes (AMP); acceptors for oxidative phosphorylation (ADP); allosteric regulators of enzyme activity; and as second messengers, the cyclic adenosine -3, 5-monophosphate and cyclic guanosine--3,5-monophosphate (Bohinski, 1987)
Chemical synthesis:For the synthesis of the type of nucleoside analogues, D-fructose was first converted to 1′,3′,4′,6′ -Tetra-O-benzoyl-β-D-fructo furanose(F1).The reason for conversion of D-fructose to (F1) was to protect the hydroxyl groups with a benzoate group which is known to be stable toward acid conditions, but are readily hydrolyzed by dilute alkaline(Iwai, 1968)
Summary
Natural nucleosides and nucleotides play a key role in many biosynthesis and regulatory processes in the living cell (Marry, 1993). 7-(1′,3′ ,4′,6′ tetra-O-benzoyl-β-D-fructo furanosyl)theophylline (F5) (1g, 1.32mmole) in 0.08M methanolic sodium methoxide (45ml).The mixture was refluxed with stirring for 1.5 hrs, neutralized with glacial acetic acid and evaporated to dryness, the residue was partitioned between water and chloroform and the aqueous phase was evaporated .to give a white powder
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